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【结 构 式】 
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【分子编号】51042 【品名】N-[3-[(7-chloro-4-quinolinyl)amino]-5-(hydroxymethyl)phenyl]-2-(1-piperidinyl)acetamide 【CA登记号】 |
【 分 子 式 】C23H25ClN4O2 【 分 子 量 】424.92996 【元素组成】C 65.01% H 5.93% Cl 8.34% N 13.18% O 7.53% |
合成路线1
该中间体在本合成路线中的序号：(V)The intermediate anilinoquinoline (III) was obtained by nucleophilic substitution of 4,7-dichloroquinoline (II) with 3,5-diaminobenzyl alcohol (I) in the presence of N-methylmorpholine. Coupling of (III) with chloroacetic acid gave the corresponding chloroacetamide (IV), which was further reacted with piperidine in DMF, yielding the piperidino acetamide (V). The benzyl alcohol function of (V) was then oxidized to aldehyde (VI) employing manganese dioxide. Finally, reductive condensation of aldehyde (VI) with morpholine in the presence of NaBH(OAc)3 furnished the title compound.
| 【1】 Delareu, S.; et al.; Synthesis and in vitro and in vivo antimalarial activity of new 4-anilinoquinolines. J Med Chem 2001, 44, 17, 2827. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 51039 | (3,5-diaminophenyl)methanol | C7H10N2O | 详情 | 详情 | |
| (II) | 38277 | 4,7-dichloroquinoline | 86-98-6 | C9H5Cl2N | 详情 | 详情 |
| (III) | 51040 | [3-amino-5-[(7-chloro-4-quinolinyl)amino]phenyl]methanol | C16H14ClN3O | 详情 | 详情 | |
| (IV) | 51041 | 2-chloro-N-[3-[(7-chloro-4-quinolinyl)amino]-5-(hydroxymethyl)phenyl]acetamide | C18H15Cl2N3O2 | 详情 | 详情 | |
| (V) | 51042 | N-[3-[(7-chloro-4-quinolinyl)amino]-5-(hydroxymethyl)phenyl]-2-(1-piperidinyl)acetamide | C23H25ClN4O2 | 详情 | 详情 | |
| (VI) | 51043 | N-[3-[(7-chloro-4-quinolinyl)amino]-5-formylphenyl]-2-(1-piperidinyl)acetamide | C23H23ClN4O2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(I)The title ester is obtained by condensation of benzyl alcohol (I) with the hexanoic acid (II) by means of DCC and DMAP in dichloromethane.
| 【1】 Biot, C.; Delarue, S.; Davioud-Chervet, E.; et al.; A prodrug from of a Plasmodium falciparum glutathione reductase inhibitor conjugated with a 4-anilinoquinoline. J Med Chem 2001, 44, 24, 4268. |